Tri-O-galloyl-shikimic acid - Compound Card

Tri-O-galloyl-shikimic acid

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Tri-O-galloyl-shikimic acid

Structure
Zoomed Structure
  • Family: Plantae - Combretaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Simple Gallate
Canonical Smiles O=C(c1cc(O)c(c(c1)O)O)O[C@H]1[C@H](OC(=O)c2cc(O)c(c(c2)O)O)CC(=C[C@H]1OC(=O)c1cc(O)c(c(c1)O)O)C(=O)O
InChI InChI=1S/C28H22O17/c29-13-1-10(2-14(30)21(13)35)26(40)43-19-7-9(25(38)39)8-20(44-27(41)11-3-15(31)22(36)16(32)4-11)24(19)45-28(42)12-5-17(33)23(37)18(34)6-12/h1-7,19-20,24,29-37H,8H2,(H,38,39)/t19-,20-,24-/m1/s1
InChIKey KRGJABLVIDOYEE-YOSAUDMPSA-N
Formula C28H22O17
HBA 16
HBD 10
MW 630.47
Rotatable Bonds 7
TPSA 298.27
LogP 1.43
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 45
Formal Charge 0
Fraction CSP3 0.14
Exact Mass 630.09
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Terminalia species Combretaceae Plantae 39992

Showing of synonyms

  • Pfundstein B, El Desouky SK, et al. (2010). Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): Characterization, quantitation and determination of antioxidant capacities. Phytochemistry,2010,71(10),1132-1148. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OC2C=CCC(OC(=O)c3ccccc3)C2OC(=O)c4ccccc4

Level: 3

Mol. Weight: 630.47 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C=CCCC2OC(=O)c3ccccc3

Level: 2

Mol. Weight: 630.47 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C=CCC(C2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 630.47 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C(CC=CC2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 630.47 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CC=CCC2

Level: 1

Mol. Weight: 630.47 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2C=CCCC2

Level: 1

Mol. Weight: 630.47 g/mol

Structure

SMILES: C1=CCCCC1

Level: 0

Mol. Weight: 630.47 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 630.47 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-6.93
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.17
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
11.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.68
Plasma Protein Binding
43.14
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.01
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-3.48
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.9
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.0
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-21792.15
Rat (Acute)
2.41
Rat (Chronic Oral)
4.0
Fathead Minnow
48.87
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Toxic

General Properties

Boiling Point
485.12
Hydration Free Energy
-3.01
Log(D) at pH=7.4
0.33
Log(P)
1.26
Log S
-4.81
Log(Vapor Pressure)
-17.29
Melting Point
291.82
pKa Acid
6.69
pKa Basic
2.81
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9245
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9245
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8870
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8870
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8788
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8788
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8630
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8630
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8567
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8567
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 3 0.8561
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 3 0.8561
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8554
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8554
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8538
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8538
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase B1MKD5 B1MKD5_MYCA9 Mycobacteroides abscessus 3 0.8520
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase B1MKD5 B1MKD5_MYCA9 Mycobacteroides abscessus 3 0.8520
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 4 0.8515
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 4 0.8515
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.8496
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 3 0.8496
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8468
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8468
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8465
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8465
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8437
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8437
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8405
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8405
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8326
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8326
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8295
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8295
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8257
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8257
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8168
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8168
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8162
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8162
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8123
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8123
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8123
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8123
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8123
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8123
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8098
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8098
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8097
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8097
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8085
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8085
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8060
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8060
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.8050
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.8050
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8040
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8040
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7825
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7825
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7802
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7802
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7786
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7786
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7769
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7769
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7715
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7715
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7697
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7697
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7688
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7688
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7658
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7658
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7601
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7601
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7531
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7531
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.7525
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.7525
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7492
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7492
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7465
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7465
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 3 0.7453
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 3 0.7453
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7401
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7401
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 3 0.7389
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 3 0.7389
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7380
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7380
Thymidylate synthase P04818 TYSY_HUMAN Homo sapiens 4 0.7346
Thymidylate synthase P04818 TYSY_HUMAN Homo sapiens 4 0.7346
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7324
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7324
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7286
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7286
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7282
Calmodulin P62157 CALM_BOVIN Bos taurus 3 0.7282
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7270
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.7270
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7252
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7252
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7196
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7196
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7164
Cytochrome P450 2C8 P10632 CP2C8_HUMAN Homo sapiens 3 0.7164
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7147
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7147
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7145
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7145
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7133
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7133
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 5 0.7131
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7131
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 5 0.7131
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7131
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7129
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7129
Ribosomal RNA small subunit methyltransferase NEP1 Q06287 NEP1_YEAST Saccharomyces cerevisiae 4 0.7129
Ribosomal RNA small subunit methyltransferase NEP1 Q06287 NEP1_YEAST Saccharomyces cerevisiae 4 0.7129
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7120
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7120
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7116
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7116
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7093
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7093
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7085
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7085
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 5 0.7082
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 5 0.7082
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7078
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7078
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7062
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7062
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7054
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7054
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 5 0.7051
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 5 0.7051
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 5 0.7049
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 5 0.7049
Histone H3 P61830 H3_YEAST Saccharomyces cerevisiae 2 0.7048
Histone H3 P61830 H3_YEAST Saccharomyces cerevisiae 2 0.7048
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7034
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7034
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7023
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7023
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7014
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7014

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